WO2008044713A1 - Dérivé de pyridinecarboxanilide substitué ou un de ses sels, agent agricole ou horticole et utilisation de celui-ci - Google Patents

Dérivé de pyridinecarboxanilide substitué ou un de ses sels, agent agricole ou horticole et utilisation de celui-ci Download PDF

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WO2008044713A1
WO2008044713A1 PCT/JP2007/069778 JP2007069778W WO2008044713A1 WO 2008044713 A1 WO2008044713 A1 WO 2008044713A1 JP 2007069778 W JP2007069778 W JP 2007069778W WO 2008044713 A1 WO2008044713 A1 WO 2008044713A1
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group
halo
alkyl
alkoxy
different
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PCT/JP2007/069778
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English (en)
Japanese (ja)
Inventor
Takashi Furuya
Hideo Kanno
Akiyuki Suwa
Noriaki Yasokawa
Shinsuke Fujioka
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Nihon Nohyaku Co., Ltd.
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Priority to JP2008538745A priority Critical patent/JPWO2008044713A1/ja
Publication of WO2008044713A1 publication Critical patent/WO2008044713A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to a substituted pyridinecarboxylic acid anilide derivative and a salt thereof, an agricultural and horticultural drug containing the compound as an active ingredient, particularly an insecticide or acaricide, and a method of using the same.
  • substituted pyridinecarboxylic acid amide derivatives similar to the present invention are useful as agricultural and horticultural insecticides, fungicides or acaricides (see, for example, Patent Documents 1 and 2).
  • the substituent of the aniline moiety is limited to the 2-position substitution product, and the compound in which an alkyl group is introduced at the 3-position described in the present invention is disclosed. Absent.
  • the substituted pyridine strength rubonic acid anilide derivatives specifically disclosed therein show acaricidal activity! /, Na! / ,.
  • the substituent of the aniline moiety is limited to an alkoxy group, and a compound in which an alkyl group is directly introduced at the 3-position described in the present invention is not disclosed. .
  • Patent Document 1 Japanese Patent Laid-Open No. 2003-48878
  • Patent Document 2 JP 2004-189738 A
  • a substituted phenoxycarbonyl group having one or more substituents selected on the ring having one or more substituents selected on the ring,
  • a substituted phenylsulfinyl group having one or more substituents selected on the ring having one or more substituents selected on the ring
  • Z represents an oxygen atom or a sulfur atom.
  • n an integer of 0 to 3.
  • X may be the same or different
  • m represents an integer of 0 to 4.
  • Y can be the same or different
  • a substituted phenyl group having one or more substituents selected on the ring having one or more substituents selected on the ring
  • One or more substituents selected on the ring can also be present on the ring.
  • C-c alkynyl “heterocyclic group” and the like have the following meanings.
  • Halogen atom refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • C 1 -C alkyl refers to a linear or branched alkyl having 1 to 6 carbon atoms.
  • C_C alkyl refers to a linear or branched alkyl having 1 to 10 carbon atoms
  • C 1 -C cycloalkyl refers to a cyclic alkyl having 3 to 6 carbon atoms, for example,
  • C 1 -C cycloalkyl refers to a cyclic alkyl having 3 to 8 carbon atoms, for example,
  • C 1 -C cycloalkyl refers to a cyclic alkyl having 3 to 10 carbon atoms
  • Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl and the like.
  • C_C cycloalkenyl refers to cyclic alkenyl having 3 to 10 carbon atoms
  • cyclopropeninore cyclobuteninore, cyclopenteninole, cyclohexenore, cyclotatur, cyclodecenyl and the like can be mentioned.
  • C 1 -C alkoxy is an alkyl moiety having 1 straight or branched carbon atoms.
  • alkoxy which is ⁇ 3 alkyls, for example, methoxy, ethoxy, propoxy, i Examples include sopropoxy.
  • C 1 -C alkoxy is an alkoxy whose alkyl moiety is the above "C 1 -C alkyl”.
  • C 1 -C alkenyl refers to a straight or branched chain having at least one double bond
  • C_C alkenyl refers to a linear or branched chain having at least one double bond
  • Alkenyl having 3 to 10 carbon atoms for example, 1-butur, 2 butur, 3 —butur, 2 pentul, 2,4 pentagenyl, 3 hexenyl, 3 heptenyl, 3 —octatur, 3—nonenole, 3-decenyl etc. are mentioned.
  • C 1 -C alkynyl is a straight chain or branched chain having at least one triple bond
  • Alkynyl having 2 to 6 carbon atoms such as Etul, 2-Probule, 1-Butul, 2 Butur, 3 Butur, 2 Pentur, 3 Hexhur, etc.
  • C_C alkynyl is a straight or branched chain having at least one triple bond.
  • alkynyl having 3 to 10 carbon atoms is exemplified, and examples thereof include 1-buturur, 2 butur, 3-butur, 2 pentur, 3 hexul, 3 heptul, 3-otatul, 3-nonynyl, 3-decynyl and the like.
  • numbers such as “C 1 -C:” and “C 2 -C” are carbon such as 2 to 6 carbon atoms, 3 to 10 carbon atoms, etc.
  • halo c-c alkyl one or more halogen atoms which may be the same or different
  • a substituted linear or branched carbon atom for example, difluoromethyl, trifluoromethyl, 2, 2, 2-trifluoroethyl, perfluorinated hexyl, etc. Can be mentioned.
  • Heterocyclic group means one or more heter selected from an oxygen atom, a sulfur atom and a nitrogen atom.
  • a 5- or 6-membered heterocyclic group having a mouth atom such as pyridyl group, pyridine N oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, chenyl group, tetrahydrophenyl group, tetrahydrobilanyl group, tetrahydro
  • Examples include thiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group and the like.
  • fused ring examples include naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indanol, indoline, chroman, isochroman, benzodioxan, benzodioxanol, benzofuran, dihydrobenzofuran, benzothiophene, dihydrin benzothiophene, Benzoxazonore, benzothiazonole, benzimidazole, indazole and the like.
  • R 1 is preferably (la) a hydrogen atom, (2a) a C_C alkyl group, (3a) a halo C 1 -C alkyl group
  • phenyl C-C alkyl group, (39a) may be the same or different
  • la may be the same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) C -C Alkynole group, ( e ) halo C-C canolequinole group, (f) C-C alkoxy group, (g) halo C-C alco
  • C-Canolenoquinamino groups (0) di-C-Canolenoquinamino groups which may be the same or different, and
  • C alkylsulfonyl group, (n) mono C 1 -C anolenoquinamino group, (0) may be the same or different
  • Enyl C 1 -C alkylcarbonyl group or (57a) same or different (a) halogen (B) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 1 -C alkyl group,
  • Norebonyl group (37a) Ciano C 1 -C alkyl group, or (49a) C _C cycloalkylcarbohydrate
  • R 2 is preferably (lb) a hydrogen atom, (2b) a halogen atom, (3b) a C_C alkyl group, (4b)
  • (7b) is a C 1 -C alkoxy group.
  • G is preferably (lc) C 1 -C alkyl group, (2c) halo C 1 -C alkyl group, (7c) C 1 -C
  • X is preferably (Id) a halogen atom, or (4d) a C 1 -C alkyl group, and more preferably Or X means no substitution, and n is 0.
  • Y is preferably (le) a halogen atom, (8e) C _C canolequinole group, (9e) halo C -C alkyl
  • 1 6 1 6 1 6 is a (30e) C 1 -C alkylthio group.
  • m is preferably 1 or 2, and more preferably 1.
  • Z is preferably an oxygen atom.
  • Examples of the salt of the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention include alkali metal (lithium, sodium, potassium, etc.) salts, alkaline earth metals (calcium, magnesium, etc.) Salts, ammonium salts, salts of organic amines (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.) or acid addition salts.
  • Acid addition salts include, for example, acetate, propionate, and salt.
  • Acid salts trifluoroacetates, benzoates and other carboxylates, methanesulfonate, trifluoromethanesulfonate, p sulfonates such as toluenesulfonate, hydrochloride, sulfate, nitrate, carbonate
  • examples include inorganic acid salts such as salts.
  • the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in the structural formula, and two or more optical isomers may be included. And diastereomers may exist, and the present invention includes all of the optical isomers and mixtures in which they are contained in an arbitrary ratio.
  • the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula. The invention includes all of the various isomers and mixtures containing them in any proportion.
  • W is — O, S or — N (R 4 )-(wherein R 4 is a hydrogen atom, C 1 -C alkyl)
  • Q represents a halogen atom or a C 1 -C alkoxy group.
  • Z is represented by an oxygen atom
  • R 2 is a hydrogen atom
  • the substituted pyridinecarboxylic acid anilide derivative (I 2) represented by general formula ( ⁇ —1) to general formula ( ⁇ —3) and the pyridine carboxylate represented by general formula (III) By reacting an acid halide or pyridinecarboxylic acid ester in the presence or absence of a base in an inert solvent, or represented by general formula ( ⁇ —1) to general formula ( ⁇ —3) Forces that can be produced by reacting an aniline derivative and a pyridinecarboxylic acid represented by the general formula (IV) in the presence of a condensing agent in the presence or absence of a base in an inert solvent. If it ’s a manufacturing method, it ’s good.
  • the aniline derivative represented by the general formula ( ⁇ -2) is produced by reducing the aniline derivative represented by the general formula (II 1) in an inert solvent in the presence of a reducing agent. Can do.
  • the aniline derivative represented by the general formula ( ⁇ -3) is represented by the general formula (V) in an inert solvent in the presence or absence of a base, the aniline derivative represented by the general formula (II 1). Produced by reacting with alcohol derivatives, thiol derivatives or amine derivatives Can do.
  • Reducing agents that can be used in this reaction include lithium metal hydride, lithium borohydride, sodium borohydride, diisobutylaluminum hydride, metal hydride such as sodium bis (2-methoxyethoxy) aluminum hydride, metal lithium
  • the metal or metal salt, etc. can be exemplified, and the amount used can be appropriately selected from the range of equivalent to excess amount with respect to the ayurin derivative represented by the general formula ( ⁇ -1). .
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, methyl chloride, chloroform, tetrachloride.
  • Inert solvents such as halogenated hydrocarbons such as carbon, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, and chain or cyclic ethers such as jetyl ether, dioxane and tetrahydrofuran (THF)
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • methyl chloride chloroform
  • tetrachloride tetrachloride
  • Inert solvents such as halogenated hydrocarbons such as carbon, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, and chain or cyclic ethers such as jetyl ether
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
  • After completion of the reaction it can be isolated from the reaction system containing the target product by a conventional method.
  • the target product can be produced by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.
  • Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and lithium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, n-butyl lithium, and s-butyl.
  • metal hydrides such as lithium hydride, sodium hydride and lithium hydride
  • metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, n-butyl lithium, and s-butyl.
  • alkyl metals such as lithium and t-butyllithium
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, and jetyl.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • alcohols such as methanol and ethanol
  • jetyl Illustrate inert solvents such as chain, cyclic ethers such as ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, etc.
  • These inert solvents can be used alone or in admixture of two or more.
  • the reaction temperature can be in the range of 70 ° C to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
  • the reaction system containing the target product After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method.
  • the target product can be produced by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.
  • the condensing agent used in this reaction for example cyanophosphonate Jechiru (DEPC), carboxymethyl sulfonyl diimidazole (CDI), 1, 3- dicyclo hexyl Cal positive imide (DCC), black hole carbonate esters, iodide 2-chloro 1
  • Examples include methylpyridinium and the like.
  • Examples of the base used in this reaction include inorganic bases and organic bases.
  • inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride, and potassium hydride.
  • Alkali metal hydrides such as sodium ethoxide, potassium t-butoxide, etc.
  • alkali metal salts such as sodium carbonate, potassium carbonate, sodium bicarbonate, etc.
  • organic bases include, for example, triethylamine, pyridine, DBU
  • the amount used may be selected from the range of equimolar to excess molar relative to the pyridinecarboxylic acid derivative represented by the general formula (III) or (IV).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, methyl chloride, and chloroform.
  • Halogenated hydrocarbons such as carbon tetrachloride, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, chain or cyclic ethers such as jetyl ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate , Amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and inert solvents such as acetone and methylethylketone. Solvents can be used alone or in combination of two or more.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the boiling point of the inert solvent used.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours.
  • An aniline derivative represented by a general formula ( ⁇ -1) can be produced according to the production method disclosed in JP-A-11-302233 or 2001-122836.
  • pyridinecarboxylic acid derivatives represented by the general formula (III) or (IV) are known literatures (for example, Industrie Chimique Beige (1967), 32, 165, JP-A-03-52862, JP-A-03). — 81263, J. Chem. Soc., Perkin Trans I, 1984, 1501, etc.) It can be produced according to the method described.
  • the substituted pyridinecarboxylic acid anilide derivative (I 3) in which ⁇ is a sulfur atom is an aniline derivative represented by (I 2). It can be produced by reacting with Lawesson's reagent according to a known method (Tetrahedron Lett., 21 (42), 4061 (1980)).
  • R 2 G, X, Y, Q, m and n are as defined above.
  • R 1 ' is the same comb in R 1, provided that a hydrogen atom is excluded.
  • a substituted pyridinecarboxylic acid anilide derivative (I 2) other than R 1 is a hydrogen atom is an amide derivative represented by the general formula (I 2a) It can be produced by reacting a halide derivative or ester derivative represented by the general formula (VI) in an inert solvent in the presence or absence of a base.
  • Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and lithium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and n-butyllithium. , S butyl lithium, t butyl lithium and the like, and the use amount thereof is appropriately selected from the range of equivalent to excess amount with respect to the amide derivative represented by the general formula (I 2a). Use it.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, and jetyl.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • alcohols such as methanol and ethanol
  • jetyl examples of the inert solvent include ethers, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, and other chain or cyclic ethers. These inert solvents may be used alone or in combination of two or more. can do.
  • the reaction temperature can be in the range of 70 ° C to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
  • the target product After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. If necessary, the target product can be produced by recrystallization, column chromatography, etc.
  • substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I-2c) is obtained by converting the sulfide derivative represented by the general formula (I 2b), which can be produced by the production method 1, with an oxidizing agent in the presence of an inert solvent. It can manufacture by making it react.
  • Examples of the inert solvent used in this reaction include halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, halogenated compounds such as fluorobenzene, chloroform benzene, and dichlorobenzene.
  • Examples thereof include aromatic hydrocarbons, acids such as acetic acid, and alcohols such as methanol, ethanol and propanol.
  • Examples of the oxidizing agent include metaclonal perbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (Oxon (registered trademark)), hydrogen peroxide, and the like.
  • the sulfur derivative represented by (I 2b) may be used by appropriately selecting from a range of 0.5 to 3 equivalents.
  • the reaction time should be in the range of 50 ° C to the boiling point of the inert solvent used, but the reaction time is not constant depending on the reaction temperature, reaction scale, etc., but is in the range of several minutes to 24 hours.
  • the product can be isolated from the reaction system containing the product according to a conventional method. If necessary, the product can be produced by recrystallization, column chromatography or the like.
  • Table 1 shows the 1 H-NMR data for.
  • n is normal, “i-” is iso, “t-” is tertiary, “c-” is cyclo, “Me” is methyl, “Et” is ethyl.
  • Pr '' is a propyl group
  • ⁇ Bu '' is a butyl group
  • ⁇ Pen '' is a pentyl group
  • Hex is a hexyl group
  • Ac is a acetyl group
  • l-Ph-c-Pr is 1 phenol cyclopropyl group, "1-6.-?” Is 1-methyl.
  • Agricultural and horticultural chemicals containing the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient particularly agricultural and horticultural insecticides or acaricides are paddy rice, fruit trees and vegetables. It is suitable for various pests such as various forests, horticulture, storage pests, sanitary pests, nematodes, and other crops that damage crops and flowers.
  • Hemiptera pests (Anomala rufocuprea), Japanese beetle (Popilla japonica), Lasioderma serricorne, Buffalo (Lyctus brunneus), Ninyuyahosian (Callosobrucnus chinensis) Listroderes costirostris, Sitophilus zeamais, Anthonomus grandis granais, Lissornoptrus oryzophnus, Rein, Aulacophora femoralis, Oulema or Oulemayz Phyllotreta striolata)
  • the substituted pyridinecarboxylic acid anilide derivative or a salt thereof represented by the general formula (I) of the present invention is preferably used as an agricultural or horticultural insecticide or an acaricide. It exhibits excellent control effects against various pests such as insect pests and sanitary pests, and can be used as a pest control agent in a wide range of fields. Examples of these pests include, for example, Rufidens Bigot, etc., Musca domestica uicina MACQUART, etc., Housefly, Gasterophilus intestinalis, etc.
  • spirocularis etc., Culex pipiens pallens, Shimano, madara force (An opheles sinensis) ⁇ Aedes japonicus, etc nocephalides felis), Meno: iACtenocepnaiides canis), Anthropaceae such as Pmex irritans, Ticks such as Ixodes ovatus Neumann, Scorpionaceae such as Euproctis similes, Sitophilus zo Vespa, Vespa simillima xanthoptera Cameron, etc. pubis), white-tailed termites (Reticulitermes speratus), termites (Copt otermes formosanus), etc .; Can be mentioned.
  • Anthropaceae such as Pmex irritans
  • Ticks such as Ixodes ovatus Neumann
  • Scorpionaceae such as Euproctis similes, Sitophilus zo Vespa, Vespa si
  • Agricultural and horticultural agents in particular, agricultural and horticultural insecticides or acaricides, containing a substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient are paddy field crops. It has a remarkable control effect against the above-mentioned pests that damage field crops, fruit trees, vegetables, other crops and flowers, etc., so that the occurrence of pests may occur before or after the occurrence of pests. When confirmed, it is treated with paddy fields, fields, fruit trees, vegetables, other crops, flower seeds, paddy water, foliage, or soil to provide the agricultural and horticultural insecticide of the present invention. The effect of the period is produced.
  • the plant that can use the agricultural and horticultural agent of the present invention is not particularly limited, and examples thereof include the following plants.
  • Saccharifera ory: 7, rubber, coffee Tanoku , Tea, etc.), potatoes (cabochia, cucumber, watermelon, melon, etc.), pastures (orchard grass, sorghum, timosi, clover, alfalfa, etc.), turf (Korea turf, bentgrass, etc.), crops for flavoring It can be used for plants such as lavender (Lavandula officinalis CHAIX), rosemary, thyme, parsley, pepper, ginger, etc., and flowers (chrysanthemum, rose, orchid, etc.).
  • genetically modified crops (herbicide-resistant crops, pest-resistant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against diseases, crops with improved taste, and preservation stability have been improved.
  • the agrochemical composition can be used in combination with these techniques or systematized.
  • the agricultural and horticultural chemicals of the present invention are generally used in a form convenient for use according to a conventional method for agricultural chemical formulations.
  • the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio.
  • an auxiliary agent in an appropriate ratio.
  • Separated, suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. And use it.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, and sawdust. , Tabacco stem powder, walnut shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg Talc, pyrophyllite, etc.), silica ⁇ eg, diatomaceous earth, silica sand, mica, white carbon (some synthetic highly dispersed silicic acid, also called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as the main component.) ⁇ , Activated charcoal, iow powder, pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, Plastic carriers vinyli
  • the material that can be used as a liquid carrier is selected from those having solvent ability itself, and those that can disperse the active ingredient compound with the aid of an auxiliary agent without having solvent ability.
  • the following carriers can be exemplified as typical examples, but these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (Eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (Eg kerosene, mineral oil), aromatic hydrocarbons (eg benzene) , Toluene
  • adjuvants typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose, and singly, in some cases, two or more kinds of adjuvants are used. Used together or In some cases it is possible to use no adjuvants at all.
  • Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylenes.
  • surfactants such as lenic resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, and higher alcohol sulfate Show power S
  • auxiliary agents such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, Adjuvants such as polybulal alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used.
  • the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used.
  • adjuvants such as waxes, stearates and alkyl phosphates
  • a peptizer for a suspension product for example, an auxiliary such as naphthalenesulfonic acid condensate or condensed phosphate is used.
  • an auxiliary agent such as silicone oil
  • silicone oil can be used as the antifoaming agent.
  • preservatives 1,2-benzisothiazoline-1-3-one, parachlorometaxylenenole, butyl noroxybenzoate and the like can also be added.
  • activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, ultraviolet absorbers, etc.
  • additives can also be added.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and it can be used by appropriately selecting from the range of 0.0;! To 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide. For example, in the case of a powder or granule, 0.0;! To 50% by weight, and in the case of an emulsion or wettable powder, 0.0;! To 50% by weight is appropriate.
  • the agricultural and horticultural chemicals of the present invention are predicted to generate pests in an effective amount for controlling pests as they are, or appropriately diluted with water or suspended to control various pests. It may be used by applying it to crops that are unfavorable or where generation is not desirable.
  • the amount of the agricultural and horticultural agent used in the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be appropriately selected according to the purpose from the range of 10 OOlg to 10 kg, preferably 0.01 g to 1 kg per 10 are.
  • the agricultural and horticultural agents of the present invention are further used for other agricultural and horticultural insecticides, acaricides, and nematicides for the purpose of expanding pests to be controlled, the appropriate control period, or reducing the dosage. It can be used in combination with herbicides, fungicides, biological pesticides, etc., and can be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
  • Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, ethion, trichlorfone, methamidophos, acephete, dichlorvos, mevinphos, monocrotofos, malati, dimethoate, formimotin, mecarbam , Nomidothion, thiomethone, disulfoton, oxydeprophos, nared, methyl parathion, fenitrothion, sianophos, propaphos, fenthion, prothiophos, profenophos, isofenphos, temefos, phentoate, dimethylvinphos, chlorfevinphos, tetrachlorvinphos, oxime, oxime, Genius, pyracrofos, methidathion, black mouth pyrifos, chlorpyrifos' methinore, pyrida
  • Agricultural and horticultural fungicides used for the same purpose include, for example, sulfur, lime sulfur mixture, basic copper sulfate, iprobenfos, edifenfos, torque port phos'methyl, tyram, polycarnomate, dinebu, Manzeb, mancozeb, propineb, thiophanate, thiophanate methyl, benomyl, iminotazine acetate, iminotazine albosylate, mepronil, phenolate, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadixil, carpropamide, diclofluanide, fursulfamide , Chlorothalonyl, Cresoxime 'Methinole, Phenoxanil, Himexazole, Etalomezonole, Funoleonoleimide, Procymidone, Vinclozoline, Iprodione, Triad
  • herbicides include, for example, darifosate, sulphosate, dalfosinate, bialaphos, butamifos, esprocarp, prosulfocarp, beven curve, pyributycarp, ashram, linuron, diemron, isouron, bensulfuron methyl, cyclosulfamuron, sinosnorephrone, pyra Zosnolevonechinore, Azimusnoreflon, Imazosnorefuron, Teninoreclonore, Araclonore, Pretiraclonore, Chlomeprop, Etobenzanide, Mefenaset, Pendimethalin, Bifenox, Acifluophene, Lactofene, Cihalo Hop Butyl , Ioxul, Bromobutide, Aloxidim, Cetoxidim, Napropamide, Indanophane
  • nuclear polyhedrosis virus granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect box virus (CPV) Entomopox virus, EPV
  • NPV nuclear polyhedrosis virus
  • GV granulosis virus
  • CPV cytoplasmic polyhedrosis virus
  • EPV insect box virus Entomopox virus
  • virus SeiHitoshi 1 J monochrome sports Riu arm 'Fimatono gum (Monacrosporium phymatophagum), Steiner Nema' Kapokapusae (Steinemema carpocapsae), Sutainanema 'Kushide (Stein ernema kushidai), Pasutsuria.
  • Bae Netoransu Pasteuria penetrans Microbial pesticides used as insecticides or nematicides such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Enore Vinia 'Erwinia carotovora ), Rickinoles' Bacillus subtilis, etc. Similar effects can be expected when used in combination with a microbial pesticide used as a fungicide, a biopesticide used as a herbicide such as Xanthomonas campestris.
  • the above is uniformly mixed and pulverized to obtain a powder.
  • Test Example 1 Acaricidal test against Tetranychus urticae
  • a 2 cm diameter kidney leaf leaf disk was placed on wet filter paper. After inoculating 10 adult female nymph mite, 50 ml of a drug solution diluted with 500 ppm and 50 ppm of a preparation containing the compound shown in Table 1 as an active ingredient was sprayed. Survival was investigated 2 days after treatment. The corrected death rate was calculated according to the following formula and judged according to the following criteria. 2 continuous operation at 25 ° C.
  • the compounds of the present invention No. 1-8—1-11, 1 22, 1 25, 1 28, 1-30—33, 1—35, 1-37—59, 1-61—78,
  • the compounds 1-80, 1-82, 1-89 and 1-90 showed A activity at both 500 ppm and 50 ppm concentrations.
  • all three control compounds showed no acaricidal activity even at a concentration of 500 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne : un dérivé de pyridinecarboxanilide substitué représenté par la formule générale (I) ou un de ses sels ; un agent agricole ou horticole comprenant le composé en tant qu'ingrédient actif ; et l'utilisation de l'agent. L'invention concerne donc un nouvel agent agricole ou horticole, notamment un pesticide ou acaricide. (I) dans laquelle R1 représente H, un alkyle, un alkylcarbonyle, un cycloalkyle, un phénylalkyle, un phénylcarbonyle, un cyanoalkyle ou analogue ; R2 représente H, un halogène, un alkyle, CN, OH, un alcoxy, un phénoxy, un phénylthio, un phénylsulfonyle ou analogue ; G représente un alkyle, un alcényle, un alcynyle, un cycloalkyle, un cycloalcényle ou analogue ; Z représente O ou S ; X représente un halogène, CN, NO2, un alkyle ou analogue ; Y représente un halogène, CN, NO2, OH, un mercapto, un amino, un carboxyle, un alkyle, un phényle, un phénoxy, un groupement hétérocyclique ou analogue ; m représente un nombre de 0 à 4 ; et n représente un nombre de 0 à 3.
PCT/JP2007/069778 2006-10-10 2007-10-10 Dérivé de pyridinecarboxanilide substitué ou un de ses sels, agent agricole ou horticole et utilisation de celui-ci WO2008044713A1 (fr)

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CN103281897A (zh) * 2010-11-05 2013-09-04 陶氏益农公司 用4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸及其盐或酯对抗苯氧基链烷酸除草剂的杂草的防治
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WO2014021468A1 (fr) * 2012-07-31 2014-02-06 住友化学株式会社 Composé amide
EP3070076A4 (fr) * 2013-11-12 2017-07-19 Nihon Nohyaku Co., Ltd. Composé amide ou son sel, produit agricole/horticole insecticide/bactéricide contenant ledit composé, et procédé pour son utilisation
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors
WO2021139370A1 (fr) * 2020-01-07 2021-07-15 沈阳化工大学 Composé amide et son application
WO2023284645A1 (fr) * 2021-07-12 2023-01-19 沈阳化工大学 Composé amide et son utilisation
US11926616B2 (en) 2018-03-08 2024-03-12 Incyte Corporation Aminopyrazine diol compounds as PI3K-γ inhibitors

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JP2004189738A (ja) * 2002-11-29 2004-07-08 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2006008675A (ja) * 2004-05-27 2006-01-12 Nippon Nohyaku Co Ltd 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法

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JP2004189738A (ja) * 2002-11-29 2004-07-08 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2006008675A (ja) * 2004-05-27 2006-01-12 Nippon Nohyaku Co Ltd 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法

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US8586751B2 (en) 2009-06-12 2013-11-19 Bristol-Myers Squibb Company Nicotinamide compounds useful as kinase modulators
CN103281897A (zh) * 2010-11-05 2013-09-04 陶氏益农公司 用4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸及其盐或酯对抗苯氧基链烷酸除草剂的杂草的防治
CN103281897B (zh) * 2010-11-05 2016-04-27 陶氏益农公司 用4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸及其盐或酯对抗苯氧基链烷酸除草剂的杂草的防治
WO2014021468A1 (fr) * 2012-07-31 2014-02-06 住友化学株式会社 Composé amide
CN104507911A (zh) * 2012-07-31 2015-04-08 住友化学株式会社 酰胺化合物
US9185910B2 (en) 2012-07-31 2015-11-17 Sumitomo Chemical Company, Limited Amide compound
JPWO2014021468A1 (ja) * 2012-07-31 2016-07-21 住友化学株式会社 アミド化合物
US9888686B2 (en) 2013-11-12 2018-02-13 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide
EP3070076A4 (fr) * 2013-11-12 2017-07-19 Nihon Nohyaku Co., Ltd. Composé amide ou son sel, produit agricole/horticole insecticide/bactéricide contenant ledit composé, et procédé pour son utilisation
US10123537B2 (en) 2013-11-12 2018-11-13 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide
US11926616B2 (en) 2018-03-08 2024-03-12 Incyte Corporation Aminopyrazine diol compounds as PI3K-γ inhibitors
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors
WO2021139370A1 (fr) * 2020-01-07 2021-07-15 沈阳化工大学 Composé amide et son application
CN113149900A (zh) * 2020-01-07 2021-07-23 沈阳化工大学 一种酰胺类化合物及其应用
CN113149900B (zh) * 2020-01-07 2023-09-15 沈阳化工大学 一种酰胺类化合物及其应用
WO2023284645A1 (fr) * 2021-07-12 2023-01-19 沈阳化工大学 Composé amide et son utilisation

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